Pyridine → HCID 67312186, compound

HRID 705481Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:4]=1[NH2:5].N1C=CC=CC=1.[C:19](Cl)([O:21][CH2:22][CH:23]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]2[C:24]1=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20]>C1COCC1>[CH:34]1[C:35]2[CH:23]([CH2:22][O:21][C:19](=[O:20])[NH:5][C:4]3[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:3]=3[O:2][CH3:1])[C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:30]=2[CH:31]=[CH:32][CH:33]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-methoxy-4-nitroaniline (3 g, 17.8 mmol) was dissolved in THF (60 ml) and pyridine (1.6 ml, 19.6 mmol) was added. The reaction mixture was cooled to 0° C. and Fmoc-Cl (5.07 g, 19.6 mmol) was added in small portions. The reaction was allowed to come to ambient temperature and held for 5 hours. The reaction mixture was concentrated under reduced pressure. The crude product was purified by recrystallisation from CH2Cl2 and MeOH to afford the title compound (6.08 g, 88%). Data: (m/z)=391 (M+H)+.

Workup

customto come to ambient temperature
concentrationThe reaction mixture was concentrated under reduced pressure
customThe crude product was purified by recrystallisation from CH2Cl2 and MeOH

Sources & evidence

ORD record: ord-3e3f9769f25143ecb26cbb9015d9b8e7
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174940B2

Reaction notes

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